By Saul Patai, Zvi Z. Rappoport
Best specialists give a contribution articles facing structural, theoretical, analytical and chemical points of the numerous useful teams containing sulphur.
Chapter 1 basic and theoretical (pages 1–100): Tova Hoz and Harold Basch
Chapter 2 Structural chemistry of organosulfur compounds (pages 101–174): Bela Rozsondai
Chapter three The conformational research of sulphur?containing earrings (pages 175–195): F. G. Riddell
Chapter four Thermochemistry of organosulphur compounds (pages 197–243): Joel F. Liebman, Kristine S. ok. Crawford and Suzanne W. Slayden
Chapter five NMR and ESR of organosulphur compounds (pages 245–291): Alan R. Bassindale and James N. Iley
Chapter 6 Mass spectra of organosulfur compounds (pages 293–337): Nico M. M. Nibbering, Steen Ingemann and Leo J. De Koning
Chapter 7 Carbon acidity because of sulfur substituents (pages 339–362): Gernot Boche, John C. W. Lohrenz, Jerzy Cioslowski and Wolfram Koch
Chapter eight Thiyl radicals (pages 363–394): C. Chatgilialoglu and M. Guerra
Chapter nine Pyrolysis of organosulphur compounds (pages 395–437): Gonzalo Martin
Chapter 10 Electrochemical habit of natural molecules containing sulfur (pages 439–493): Jacques Simonet
Chapter eleven Syntheses and makes use of of isotopically labelled compounds with sulphur?containing practical teams (pages 495–597): Mieczyslaw Zielinski and Marianna Kanska
Chapter 12 delicate steel ion?promoted reactions of organo?sulphur compounds (pages 599–631): D. P. N. Satchell and R. S. Satchell
Chapter thirteen Thiol—disulfide interchange (pages 633–658): Rajeeva Singh and George M. Whitesides
Chapter 14 Vinyl sulfides (pages 659–797): Boris A. Trofimov and Bagrat A. Shainyan
Chapter 15 High?coordinated sulfur compounds (pages 799–956): Jozef Drabowicz and Piotrlly?zwa Marian Mikoljczyk
Chapter sixteen organic job of sulfoxides and sulfones (pages 957–973): Asher Kalir and Henry H. Kalir
Chapter 17 natural sulfur within the geosphere: research, constructions and chemical procedures (pages 975–1032): Eitan B. Krein
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Additional info for Sulphur-Containing Functional Groups (1993)
General and theoretical FIGURE 33. C,H,S(O)OH, structure 98 in Tables 25-27 FIGURE 34. Hoz and H. Basch FIGURE 35. C6H,S(02)H, structure 100 in Tables 25-27 FIGURE 36. C6H,S0,0H, structure 101 in Tables 25-27 1. General and theoretical FIGURE 37. C6H,S0,NH, I, structure 102 in Tables 25-27 49 50 T. Hoz and H. Basch The geometric structures of the PhSOzX compounds can be characterized by both the spatial/conformational relationship between the nuclear SOz group and the Y substituent, and the orientation of the SO, group relative to the aromatic ring.
In a Valence Bond language, CH, can form a partial double bond with the central sulphur atom if one of the other sulphur bonds (to 0 or X) is ruptured. The S-X bond is usually weaker than S=O and, being parallel to the radical MO, is well oriented for inducing such an incipient partial double-bonded structure of sulphur with methylene. The S-X bond is therefore expected to be weakened (and longer) in the radical relative to the neutral parent compound. These opposing shortening and lengthening effects for the S-X bond apparently are either individually not significant or approximately cancel each other since the S-X bond lengths remain essentially unchanged with hydrogen atom dissociation.
As expected, the more electronegative the nature of X, the easier (in terms of energy) is proton removal relative to radical formation, for breaking either the S-H and the 0-H bonds. Homolytic and heterolytic 0-H dissociation will be discussed in more detail later. 26 T. Hoz and H. Basch Tables 12 and 13 also allow a more extensive comparison of properties such as bond lengths and atomic charges in going from the sulphinic acids to the dissociated radicals and anions, along the lines discussed somewhat in Reference 1 for sulphinic compounds and derivatives and, more extensively, in Reference 2 for sulphones.